Participants
| Role | Name | HCID | Charge |
|---|
| Reactant | Hydrochloric Acid | HCID 313 | — |
| Reactant | 5H,6H,7H,8H-imidazo(1,5-a)pyridin-8-one | HCID 16752069 | — |
| Reactant | ((5-Bromo-2-iodobenzyl)oxy)(tert-butyl)dimethylsilane | HCID 68614586 | — |
| Reactant | HCID 178418918 | HCID 178418918 | — |
| Solvent | Dichloromethane | HCID 6344 | — |
| Solvent | Tetrahydrofuran | HCID 8028 | — |
| Product | HCID 68615965 | HCID 68615965 | — |
Reaction Steps
A solution of 6.55 mmol of (5-bromo-2-iodo-benzyloxy)-tert-butyl-dimethyl-silane in 20 ml of tetrahydrofuran is cooled to −20° C. 6.55 mmol of an isopropymagnesium chloride solution (2M in tetrahydrofuran) is added dropwise and stirring continued for 1 h at −20° C. A solution of 4.37 mmol of 6,7-dihydro-5H-imidazo[1,5-a]pyridin-8-one [426219-51-4] in 40 ml of tetrahydrofuran is added dropwise and the reaction mixture stirred for 40 minutes at −20° C. The reaction mixture is poured into a mixture of 0.1N aqueous HCl and dichloromethane and the layers are separated. The aqueous layer is basified with sodium bicarbonate and extracted with ethyl acetate. The combined organic layers are dried over sodium sulfate, filtered and concentrated under reduced pressure. The title compound is obtained as a white foam and used for the next step without further purification. Rt=4.61 (gradient II).
Provenance & Evidence
| DOI | 10.6084/m9.figshare.5104873.v1 |
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| Patent number | US08324235B2 |
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| Source dataset | uspto-grants-2012_12 |
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| ORD ID | ord-ee859687df7943028844e15275268c41 |
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| Source note | uspto-grants-2012_12 |
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